107 total properties
Did you mean the neighborhood Winter Park?
View 1221 RICHMOND ROAD Winter Park, FL MLS# O6365952
$19,000
5

Beds

5.1

Baths

5,164

Sq.Ft.

1221 RICHMOND ROAD

Winter Park, FL

Courtesy of LA ROSA REALTY LLC
View 3651 N GOLDENROD ROAD D201 Winter Park, FL MLS# O6361625
$1,625
2

Beds

2.0

Baths

840

Sq.Ft.

3651 N GOLDENROD ROAD D201

Winter Park, FL

Courtesy of VESTI LLC
View 2183 CRANDON AVENUE 1/2 Winter Park, FL MLS# O6365087
$1,295
2

Beds

1.0

Baths

600

Sq.Ft.

2183 CRANDON AVENUE 1/2

Winter Park, FL

Courtesy of REAL PROPERTY MANAGEMENT AND REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1041 ARAGON AVENUE Winter Park, FL MLS# TB8453961
$2,500
2

Beds

2.1

Baths

1,641

Sq.Ft.

1041 ARAGON AVENUE

Winter Park, FL

Courtesy of BANNER INT'L REAL ESTATE
View 1095 W MORSE BOULEVARD 101 Winter Park, FL MLS# O6365507
$56,028
5,282

Sq.Ft.

1095 W MORSE BOULEVARD 101

Winter Park, FL

Courtesy of DEBORAH E GARSON PA
View 250 CAROLINA AVENUE 307 Winter Park, FL MLS# O6365311
$1,950
1

Beds

2.0

Baths

1,153

Sq.Ft.

250 CAROLINA AVENUE 307

Winter Park, FL

Courtesy of VERANDA PARK REALTY LLC
View 3060 GEORGE MASON AVENUE 10C Winter Park, FL MLS# O6365124
$1,300
1

Beds

1.0

Baths

803

Sq.Ft.

3060 GEORGE MASON AVENUE 10C

Winter Park, FL

Courtesy of PRISTINE INTERNATIONAL REALTY LLC
View 650 TRINIDAD COURT 650 Winter Park, FL MLS# O6364866
$1,750
2

Beds

2.0

Baths

1,120

Sq.Ft.

650 TRINIDAD COURT 650

Winter Park, FL

Courtesy of TRUSTHOME PROPERTIES INC
View 1400 S PENNSYLVANIA AVENUE Winter Park, FL MLS# TB8452820
  • Adult Community with Virtual Tour
1 of 8
$7,000
4

Beds

3.0

Baths

2,310

Sq.Ft.

1400 S PENNSYLVANIA AVENUE

Winter Park, FL

Courtesy of JACK KELLER INC
View 1275 MICHIGAN AVENUE Winter Park, FL MLS# O6362243
$3,950
3

Beds

2.1

Baths

1,866

Sq.Ft.

1275 MICHIGAN AVENUE

Winter Park, FL

Courtesy of COMPASS FLORIDA LLC
View 3197 CROWN JEWEL COURT Winter Park, FL MLS# O6364119
$1,995
3

Beds

2.1

Baths

1,442

Sq.Ft.

3197 CROWN JEWEL COURT

Winter Park, FL

Courtesy of FLORIDA REALTY INVESTMENTS
View 151 N ORLANDO AVENUE 226 Winter Park, FL MLS# O6364336
$2,150
2

Beds

1.0

Baths

768

Sq.Ft.

151 N ORLANDO AVENUE 226

Winter Park, FL

Courtesy of LOKATION
View 200 ST ANDREWS BOULEVARD 601 Winter Park, FL MLS# O6364892
$1,400
1

Beds

1.0

Baths

727

Sq.Ft.

200 ST ANDREWS BOULEVARD 601

Winter Park, FL

Courtesy of HOST MANAGEMENT GROUP LLC
View 2250 LEE ROAD 206 Winter Park, FL MLS# O6363122
  • Virtual Tour
1 of 36
$29,943
17,600

Sq.Ft.

2250 LEE ROAD 206

Winter Park, FL

Courtesy of INNOVATIVE REALTY, LLC
View 332 HARRIS AVENUE Winter Park, FL MLS# O6363249
  • Virtual Tour
1 of 49
$3,000
3

Beds

2.0

Baths

1,392

Sq.Ft.

332 HARRIS AVENUE

Winter Park, FL

Courtesy of UNITED REAL ESTATE PREFERRED
View 2948 ANTIQUE OAKS CIRCLE 94 Winter Park, FL MLS# O6363775
$1,250
1

Beds

1.0

Baths

749

Sq.Ft.

2948 ANTIQUE OAKS CIRCLE 94

Winter Park, FL

Courtesy of THE PAMPAS REAL ESTATE GROUP, LLC.
View 730 W SWOOPE AVENUE Winter Park, FL MLS# O6362255
  • Virtual Tour
1 of 72
$3,700
5

Beds

3.0

Baths

2,132

Sq.Ft.

730 W SWOOPE AVENUE

Winter Park, FL

Courtesy of LPT REALTY, LLC
View 1690 DALE AVENUE Winter Park, FL MLS# R4910293
  • Virtual Tour
1 of 11
$3,800
4

Beds

2.0

Baths

1,474

Sq.Ft.

1690 DALE AVENUE

Winter Park, FL

Courtesy of ZAMIN INC
View 1502 MICHIGAN AVENUE B Winter Park, FL MLS# O6355069
$1,399
2

Beds

1.0

Baths

660

Sq.Ft.

1502 MICHIGAN AVENUE B

Winter Park, FL

Courtesy of 407 PROPERTIES
View 2809 BOWER ROAD Winter Park, FL MLS# R4910253
  • Virtual Tour
1 of 29
$2,995
3

Beds

2.0

Baths

1,488

Sq.Ft.

2809 BOWER ROAD

Winter Park, FL

Courtesy of STRAWBERRY FIELDS FOREVER REALY LLC

About Winter Park

Long considered one of the most desirable addresses in Central Florida, Winter Park has been experiencing a wave of new construction along with revitalization of historic areas.  In some instances, developers are choosing to raze older buildings and replace them with luxurious new homes, some that surpass the $1 million price range.  Handsome new residential villages can include exceptional amenities like lakefront parks, pools, and nature preserves.  Winter Park offers a number of amenities that are unusual for a smaller town, including the Rollins College.  This highly respected, private, liberal arts college with its lush campus enriches the entire community educationally, culturally, and economically.  However, the college is not the town's only point of pride.  One of the world's most comprehensive collections of the works of Louis Comfort Tiffany is permanently housed in the Charles Hosmer Morse Museum of American Art.  Aficionados of shopping are drawn to Park Avenue, a quaint district where an oak-shaded park and bandstand are surrounded by art galleries, museums, clothing stores, retail outlets, and wonderful boutiques.  

Listings in Winter Park, FL

280

Estimated median home price

$675,000
Winter Park FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winter Park, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winter Park, FL.

Homes for Sale by Price in Winter Park, FL

Price Count
$0 - 100K 6
$100K - 200K 37
$200K - 300K 19
$300K - 400K 16
$400K - 500K 25
$500K - 600K 22
$600K - 700K 21
$700K - 800K 21
$800K - 900K 4
$900K - 1M 11
$1M - Max 98

Homes for Sale by Type in Winter Park, FL

Property Type Count
Single Family 162
Townhouse 19
Condo 70
Commercial 4
Rental 107
Lots and Land 20
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 1/2/2026)

Information deemed reliable but not guaranteed.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 1/2/2026.